Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

0425628 - ÚVGZ 2014 RIV CH eng J - Journal Article
Kos, J. - Zadražilová, I. - Pesko, M. - Keltosova, S. - Tengler, J. - Goněc, T. - Bobál, P. - Kauerová, T. - Oravec, Michal - Kolař, P. - Čížek, A. - Králová, K. - Jampílek, J.
Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides.
Molecules. Roč. 18, č. 7 (2013), s. 7977-7997. E-ISSN 1420-3049
R&D Projects: GA MŠMT(CZ) ED1.1.00/02.0073
Institutional support: RVO:67179843
Keywords : hydroxynaphthalene-2-carboxanilides * lipophilicity * photosynthetic electron transport inhibition * spinach chloroplasts * in vitro antibacterial activity * in vitro antimycobacterial activity * in vitro cytotoxicity * structure-activity relationships
Subject RIV: EH - Ecology, Behaviour
Impact factor: 2.095, year: 2013

In this study, a series of twenty-two ring-substituted 3-hydroxy-N-phenylnaphthalene-2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 mu mol/L) against S. aureus as well as methicillin-resistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2-carboxamide showed higher activity (MIC = 28.4 mu mol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl) naphthalene-2-carboxamide expressed higher activity (MIC = 13.0 mu mol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 mu mol/L. The structure-activity relationships of all compounds are discussed.
Permanent Link: http://hdl.handle.net/11104/0231483